Dyestuffs and process of making same



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ALVIN S. WHEELER, OF'CHAPEL HILL, NORTH CAROLINA.

DYESTUFFS AND PROCESS QF MAKING SAME.

No Drawing.

To all whom it may concern:

Be it known that I, ALVIN S. \VHEELER, a citizen of the United States, residing at Chapel Hill, in the county of ()range and State of North Carolina, have invented certain new and useful Improvements in Dyestuffs and Process of Making blame, of which the following is a specification.

By the halogenation ot' juglon (5-hydroxy-a-nap'lithoqiiinone) and other monoand dihydrogynaphthoquinones there are obtained halogen substitution products which are phenolic in character and which dissolve in alkalis forming new and valuthe formula ()n grinding, the crystals form a brick-red powder. The melting point of this 2, 3, S trioroni-5-hydroxynaplithoquinone is about 170 It is insoluble in water but may be recrystallized from hot glacial acetic acid and may also be purified by dissolving in chloroform and precipitating with additions of light petroleum distillates.

The sodium salt of the above tribrom compound may be made by dissolving the compound in ether and shaking this solution with an aqueous solution of two parts by weight of anhydrous sodium carbonate. A purplish deposit having the formula H (),,Br,,1\*a quickly separates out. The sodium salt is soluble in water and acts as a powertul dye. Sill: is dyed directly a beautiful champagne color which may be modified by the use of mordants. Wool is also dyed directly in shades of tan. Cotton 15 not dyed Specification of Letters Patent.

Application filed December 9, 1918.

Patented Jan e, LJZU.

Serial No. 265,988.

directly but when mordanted with ta-nnic acid, a light corn is obtained.

Example II: An, excess of chloriir is passed into a solution of jugloii in ten parts by weight of glacial acetic acid. After heating by steam heat for three hours, the solution is cooled and the chlorinated product is obtained in the form oi golden brown .crystals which substantially correspond to the formula This compound, diclilorojuglon, has the formula (J I'LO Gland melts at about 149 C. It is insoluble in water but soluble in alcohol, from which it may be recrystallized. The chlorinated product is also soluble iii alkalis forming a dyestutt' similar in properties to that obtained by bromination.

Dyestuli's made in accordance withmy iiivention exhibit excellent fastness toward light and laundrying. \Vhile in the foregoing examples. acetic acid is me ioued as the solvent, sodium ca rbonate the-alkali, and bronun and chlorni as the halogens, it is to be understood that the invention is not limited to the use of these agents but other plo ved, and that where these elements 'are specifically mentioned, it is for the purpose of illustration, and the invention is therefore claimed within the legitimate and valid scope of the appended claims.

Having thus described my invention, I claim 1. The process of preparing dyestuffs which comprises dissolving a hydroxynaphtlioquinono having less than three hydroxvl groups in a solvent, treating the solution with a halogen in excess, separating the halogenated product, and forming a salt thereof, substantially as described.

The process of preparing dyestuffs which comprises dissolving juglon in. hot glacial acetic acid, treating the solution with an excess of bromin, cooiing thesolution to separate the dye-base, and forming a salt of the dye-base, substantially as described.

3. As new dyestu-tiis the products resulting from the action of.. .ftlogens in excess on disformula Br u/ OH O substantially as described.

5. As, a new dyestufi', the precipitated product of bromin and jugloh corresponding substantially to the formula 6. As a new dyestufi', the deposit effected by. dissolving in ether in the presence of an alkali the crystalline product resulting from the halogenation or a hydroxynaphthoquinone. i 7. As a new dyestutl', the halogen substitution products of phenolic character and dissolvable in alkalis resulting from the halogenation of hydroxynap'hthoquinones.

8. The process of preparing dyestuffs,

comprising adding bromin to a solution of juglon, dissolving the resulting crystalline ing to the formula product in ether and adding sodium carbonate to produce a deposit substantially agree- C H O B1' Na.

9. The process of preparing dyestuffs comprising adding bromin to a solution of juglon, dissolving the resulting. crystalline product in ether, adding sodium carbonate and treating the resulting product with tannic acid. 7

10. The process of preparing dyestuffs comprising dissolving a hydroxynaphthoquinone in acetic acid, treating the solution with a halogen, heating and subsequently cooling the solution to separate the dye base, and forming a salt thereof.

11. The process of preparing dyestuffs comprising dissolving quinone in a solvent, treating the solution with a halogen, and separating the halogenated product for use as a dye base, substantially as specified.

12. Theprocess of preparing dyestuffs comprising dissolving a hydroxynaphthoquinone in a solvent, treating the solution with a halogen, separating the halogenated product, and dissolving the separated halogenated product in the presence of an alkali, substantially as specified.

13. The process of preparing dyestuffs, comprising dissolving a hydroxynaphthoquinone in a solvent, treating the solution with a halogen, separating the halogenated prod not, and associating a solution of the sepa rated product with a mordant of tannic acid, substantially as specified.

.In testimony whereof, I have hereunto set my hand this 3d day of December A. D. 1918.

ALVIN S. WHEELER. Witnesses:

CHAS. T. WOOLLEN, JA Es M. BELL.

a hydroxynaphtho- 

